N-Methyltyramine (BioDeep_00000004921)

 

Secondary id: BioDeep_00000403168, BioDeep_00000865892

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite natural product


代谢物信息卡片


4-Hydroxy-N-methylphenethylamine

化学式: C9H13NO (151.0997)
中文名称: N-甲基酪胺, 4-[2-(甲基氨基)乙基]苯酚
谱图信息: 最多检出来源 Homo sapiens(otcml) 8.71%

分子结构信息

SMILES: c1c(ccc(c1)CCNC)O
InChI: InChI=1S/C9H13NO/c1-10-7-6-8-2-4-9(11)5-3-8/h2-5,10-11H,6-7H2,1H3

描述信息

N-methyltyramine (NMT) is a phenolic amine. NMT is a potent stimulant of gastrin release present in alcoholic beverages produced by alcoholic fermentation, but not by distillation (i.e.: beer.). NMT is well absorbed in the small intestine, especially in the duodenum and jejunum. NMT is metabolized in the liver (the site of first-pass metabolism), but not in the small-intestinal mucosa. NMT is occasionally present in the stools of children and infants. Satisfactory results have been obtained in treating infective shock with injection of natural Fructus Aurantii immaturus (nat-FAI); the anti-shock effective compositions in FAI have been proved to be synephrine and NMT. (PMID: 10772638, 2570680).
Present in germinating barley roots but not dormant grainsand is also present in dormant sawa millet seed hulls, but not hulled seeds. Alkaloid from prosso millet (Panicum miliaceum)

同义名列表

20 个代谢物同义名

4-Hydroxy-N-methylphenethylamine; {p-[2-(methylamino)ethyl]phenol}; 4-[2-(Methylamino)ethyl]-phenol; 4-(2-(Methylamino)ethyl)-phenol; p-[2-(Methylamino)ethyl]-phenol; Methyl-4-tyramine hydrochloride; p-(2-(Methylamino)ethyl)phenol; Methyl-4-tyramine hydrobromide; 4-[2-(Methylamino)ethyl]phenol; 4-(2-Methylaminoethyl)phenol; p-(2-Methylaminoethyl)phenol; N-Methyl-p-tyramine; N-Methyltyraminium; N-Methyltyrosamine; Methyl-4-tyramine; N-Methyltyramine; Methyl tyramine; NMT; N-Methyltyramine; N-Methyltyramine



数据库引用编号

18 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

154 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 1 APOE
Peripheral membrane protein 1 ACHE
Endoplasmic reticulum membrane 1 TAAR1
Nucleus 2 ACHE, APOE
cytosol 2 APOA1, CCKAR
dendrite 2 APOE, DRD2
nucleoplasm 1 CCKAR
Cell membrane 10 ACHE, ADRB3, CCKBR, DRD2, TAAR1, TAAR2, TAAR5, TAAR6, TAAR8, TAAR9
Multi-pass membrane protein 11 ADRB3, ATP4A, CCKBR, DRD2, TAAR1, TAAR2, TAAR5, TAAR6, TAAR8, TAAR9, UCP1
Golgi apparatus membrane 1 DRD2
Synapse 2 ACHE, DRD2
cell surface 1 ACHE
glutamatergic synapse 2 APOE, DRD2
Golgi apparatus 2 ACHE, APOE
Golgi membrane 2 DRD2, INS
mitochondrial inner membrane 1 UCP1
neuromuscular junction 1 ACHE
neuronal cell body 1 APOE
presynaptic membrane 1 DRD2
acrosomal vesicle 1 DRD2
plasma membrane 14 ACHE, ADRB3, APOA1, APOE, ATP4A, CCKAR, CCKBR, DRD2, TAAR1, TAAR2, TAAR5, TAAR6, TAAR8, TAAR9
synaptic vesicle membrane 1 DRD2
Membrane 5 ACHE, APOE, ATP4A, CCKAR, CCKBR
apical plasma membrane 1 ATP4A
axon 2 CCK, DRD2
extracellular exosome 2 APOA1, APOE
endoplasmic reticulum 1 APOE
extracellular space 7 ACHE, APOA1, APOE, ATP4A, CCK, GAST, INS
perinuclear region of cytoplasm 1 ACHE
mitochondrion 1 UCP1
intracellular membrane-bounded organelle 1 CCKBR
Secreted 6 ACHE, APOA1, APOE, CCK, GAST, INS
extracellular region 6 ACHE, APOA1, APOE, CCK, GAST, INS
Extracellular side 1 ACHE
ciliary membrane 1 DRD2
Endosome, multivesicular body 1 APOE
Extracellular vesicle 2 APOA1, APOE
Secreted, extracellular space, extracellular matrix 1 APOE
chylomicron 2 APOA1, APOE
high-density lipoprotein particle 2 APOA1, APOE
low-density lipoprotein particle 2 APOA1, APOE
multivesicular body 1 APOE
very-low-density lipoprotein particle 2 APOA1, APOE
dendritic spine 1 DRD2
perikaryon 1 DRD2
cytoplasmic vesicle 1 APOA1
Early endosome 2 APOA1, APOE
postsynaptic membrane 1 DRD2
Apical cell membrane 1 ATP4A
Mitochondrion inner membrane 1 UCP1
GABA-ergic synapse 1 DRD2
extracellular matrix 1 APOE
basement membrane 1 ACHE
collagen-containing extracellular matrix 2 APOA1, APOE
lateral plasma membrane 1 DRD2
receptor complex 1 ADRB3
cilium 1 DRD2
Secreted, extracellular space 1 APOE
blood microparticle 2 APOA1, APOE
non-motile cilium 1 DRD2
Lipid-anchor, GPI-anchor 1 ACHE
sperm flagellum 1 DRD2
Endomembrane system 1 TAAR1
endosome lumen 1 INS
Melanosome 1 APOE
side of membrane 1 ACHE
secretory granule lumen 2 APOA1, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 APOA1, APOE, INS
axon terminus 1 DRD2
endocytic vesicle 2 APOA1, DRD2
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
clathrin-coated endocytic vesicle membrane 1 APOE
synaptic cleft 2 ACHE, APOE
dopaminergic synapse 1 DRD2
discoidal high-density lipoprotein particle 1 APOE
spherical high-density lipoprotein particle 1 APOA1
endocytic vesicle lumen 2 APOA1, APOE
chylomicron remnant 1 APOE
intermediate-density lipoprotein particle 1 APOE
lipoprotein particle 1 APOE
multivesicular body, internal vesicle 1 APOE
G protein-coupled receptor complex 1 DRD2
potassium:proton exchanging ATPase complex 1 ATP4A
[Isoform H]: Cell membrane 1 ACHE


文献列表

  • Christian Carpéné, Pénélope Viana, Jessica Fontaine, Henrik Laurell, Jean-Louis Grolleau. Multiple Direct Effects of the Dietary Protoalkaloid N-Methyltyramine in Human Adipocytes. Nutrients. 2022 Jul; 14(15):. doi: 10.3390/nu14153118. [PMID: 35956295]
  • Mélanie Leroux, Tristan Lemery, Nathalie Boulet, Anaïs Briot, Alexia Zakaroff, Anne Bouloumié, Fernando Andrade, Patricia Pérez-Matute, Jose M Arbones-Mainar, Christian Carpéné. Effects of the amino acid derivatives, β-hydroxy-β-methylbutyrate, taurine, and N-methyltyramine, on triacylglycerol breakdown in fat cells. Journal of physiology and biochemistry. 2019 Aug; 75(3):263-273. doi: 10.1007/s13105-019-00677-5. [PMID: 30919256]
  • Jianan Ni, Yingying Guo, Nianwei Chang, Dandan Cheng, Menglin Yan, Min Jiang, Gang Bai. Effect of N-methyltyramine on the regulation of adrenergic receptors via enzymatic epinephrine synthesis for the treatment of gastrointestinal disorders. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2019 Mar; 111(?):1393-1398. doi: 10.1016/j.biopha.2018.12.145. [PMID: 30841454]
  • Nianwei Chang, Yanmei Li, Mengge Zhou, Jie Gao, Yuanyuan Hou, Min Jiang, Gang Bai. The hemostatic effect study of Cirsium setosum on regulating α1-ARs via mediating norepinephrine synthesis by enzyme catalysis. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2017 Mar; 87(?):698-704. doi: 10.1016/j.biopha.2017.01.022. [PMID: 28088737]
  • Árpád Könczöl, Kata Rendes, Miklós Dékány, Judit Müller, Eszter Riethmüller, György Tibor Balogh. Blood-brain barrier specific permeability assay reveals N-methylated tyramine derivatives in standardised leaf extracts and herbal products of Ginkgo biloba. Journal of pharmaceutical and biomedical analysis. 2016 Nov; 131(?):167-174. doi: 10.1016/j.jpba.2016.08.032. [PMID: 27592255]
  • Sidney J Stohs, Michael J Hartman. A review of the receptor binding and pharmacological effects of N-methyltyramine. Phytotherapy research : PTR. 2015 Jan; 29(1):14-6. doi: 10.1002/ptr.5231. [PMID: 25274429]
  • Josep Mercader, Estelle Wanecq, Jian Chen, Christian Carpéné. Isopropylnorsynephrine is a stronger lipolytic agent in human adipocytes than synephrine and other amines present in Citrus aurantium. Journal of physiology and biochemistry. 2011 Sep; 67(3):443-52. doi: 10.1007/s13105-011-0078-2. [PMID: 21336650]
  • Federica Pellati, Stefania Benvenuti. Fast high-performance liquid chromatography analysis of phenethylamine alkaloids in Citrus natural products on a pentafluorophenylpropyl stationary phase. Journal of chromatography. A. 2007 Sep; 1165(1-2):58-66. doi: 10.1016/j.chroma.2007.07.041. [PMID: 17675045]
  • Karsten Putzbach, Catherine A Rimmer, Katherine E Sharpless, Stephen A Wise, Lane C Sander. Determination of bitter orange alkaloids in dietary supplement Standard Reference Materials by liquid chromatography with atmospheric-pressure ionization mass spectrometry. Analytical and bioanalytical chemistry. 2007 Sep; 389(1):197-205. doi: 10.1007/s00216-007-1409-6. [PMID: 17579842]
  • Federica Pellati, Stefania Benvenuti. Chromatographic and electrophoretic methods for the analysis of phenethylamine [corrected] alkaloids in Citrus aurantium. Journal of chromatography. A. 2007 Aug; 1161(1-2):71-88. doi: 10.1016/j.chroma.2007.05.097. [PMID: 17582424]
  • Lili Zhou, Andrew A Hopkins, David V Huhman, Lloyd W Sumner. Efficient and sensitive method for quantitative analysis of alkaloids in hardinggrass (Phalaris aquatica L.). Journal of agricultural and food chemistry. 2006 Dec; 54(25):9287-91. doi: 10.1021/jf061819k. [PMID: 17147408]
  • C A Bourke, S M Colegate, R A Culvenor. Evidence that N-methyltyramine does not cause Phalaris aquatica-related sudden death in ruminants. Australian veterinary journal. 2006 Dec; 84(12):426-7. doi: 10.1111/j.1751-0813.2006.00075.x. [PMID: 17156323]
  • A M El-Shazly, G Dora, M Wink. Alkaloids of Haloxylon salicornicum (Moq.) Bunge ex Boiss. (Chenopodiaceae). Die Pharmazie. 2005 Dec; 60(12):949-52. doi: . [PMID: 16398274]
  • Xian-duan Li, Zhi-jing Ma, Sheng Lin, Xue-zhu Gu, Shu-jie Mao. [Determination of synephrine and N-methyltyramine in Pericarpium Citri Reticulatae viride by HPLC]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2004 Jun; 29(6):537-9. doi: . [PMID: 15706918]
  • T Kimura, N Iwasaki, J I Yokoe, S Haruta, Y Yokoo, K I Ogawara, K Higaki. Analysis and prediction of absorption profile including hepatic first-pass metabolism of N-methyltyramine, a potent stimulant of gastrin release present in beer, after oral ingestion in rats by gastrointestinal-transit-absorption model. Drug metabolism and disposition: the biological fate of chemicals. 2000 May; 28(5):577-81. doi: . [PMID: 10772638]
  • W Kemmerling. Toxicity of Palicourea marcgravii: combined effects of fluoroacetate, N-methyltyramine and 2-methyltetrahydro-beta-carboline. Zeitschrift fur Naturforschung. C, Journal of biosciences. 1996 Jan; 51(1-2):59-64. doi: 10.1515/znc-1996-1-211. [PMID: 8721213]
  • H Hai, Z G Guo, J M Wang. Disposition of N-methyl-[ring-3,5-3H]tyramine in rabbits and mice. Zhongguo yao li xue bao = Acta pharmacologica Sinica. 1989 Jan; 10(1):41-5. doi: NULL. [PMID: 2816400]
  • Y K Huang. [Clinical observation on synephrine and N-methyltyramine in the treatment of 53 cases with shock]. Zhong xi yi jie he za zhi = Chinese journal of modern developments in traditional medicine. 1984 Feb; 4(2):95-6. doi: ". [PMID: 6235052]